Synthesis and antibacterial activity of conjugates between norfloxacin and analogues of the siderophore vanchrobactin

Souto, Alba; Montaos, Marcos A.; Balado, Miguel; Osorio, Carlos R.; Rodrı́guez, Jaime; Lemos, Manuel L.; Jiménez, Carlos

doi:10.1016/j.bmc.2012.10.028

Cited by 37 publications

(22 citation statements)

References 27 publications

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“…These molecules are key virulence factors for the fish pathogen V. anguillarum [ 144 , 145 ]. A promising aquaculture antibiotic has been developed based on synthetic conjugates of the antibiotic norfloxacin and vanchrobactin derivatives, based on the hypothesis that siderophore uptake can overcome antibiotic resistance through efflux [ 146 ]. Anguibactin is also uncommon amongst microbial siderophores for its ability to complex with gallium(III) in addition to iron [ 147 ].…”

Section: Gammaproteobacteriamentioning

confidence: 99%

Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies

2017

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Abstract:The phylum proteobacteria contains a wide array of Gram-negative marine bacteria. With recent advances in genomic sequencing, genome analysis, and analytical chemistry techniques, a whole host of information is being revealed about the primary and secondary metabolism of marine proteobacteria. This has led to the discovery of a growing number of medically relevant natural products, including novel leads for the treatment of multidrug-resistant Staphylococcus aureus (MRSA) and cancer. Of equal interest, marine proteobacteria produce natural products whose structure and biosynthetic mechanisms differ from those of their terrestrial and actinobacterial counterparts. Notable features of secondary metabolites produced by marine proteobacteria include halogenation, sulfur-containing heterocycles, non-ribosomal peptides, and polyketides with unusual biosynthetic logic. As advances are made in the technology associated with functional genomics, such as computational sequence analysis, targeted DNA manipulation, and heterologous expression, it has become easier to probe the mechanisms for natural product biosynthesis. This review will focus on genomics driven approaches to understanding the biosynthetic mechanisms for natural products produced by marine proteobacteria.

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Section: Gammaproteobacteriamentioning

confidence: 99%

Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies

2017

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“…Further, the iron coordination efficacy was compared to the natural monocatecholate siderophore Vanchrobactin ,. In particular compound 13 was found to possess a comparable Fe III affinity.…”

Section: Resultsmentioning

confidence: 99%

Bacterial RNAP Inhibitors: Synthesis and Evaluation of Prodrugs of Aryl‐ureidothiophene‐carboxylic acids

et al. 2017

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Recently, aryl‐ureidothiophene carboxylates were shown to inhibit the RNA polymerase and reduce the growth of Gram positive bacteria. We now aimed to extend the efficacy spectrum and address presumed permeation deficiencies of these agents by applying different prodrug‐approaches. Chemical syntheses yielded 12 prodrugs of three different categories featuring neutral, cationic and FeIII ‐coordinating properties. Their promising characteristics regarding stabilities, enzyme‐activation and iron coordination performance encouraged their study in growth inhibition assays of different Gram positive and Gram negative bacterial strains. These studies pointed to a positively charged, choline‐like motif being beneficial for these compounds especially for Gram‐negative bacterial cell growth inhibition.

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“…The conjugate was observed to be less effective in antibacterial effect than the parent molecule unconjugated norfloxacin (Souto et al . ). In this study, enhanced antibacterial effect of norfloxacin salts against SA‐1199B implies that the improved norfloxacin salts remain unaffected neither by efflux nor by GrlA mutation which hinders interaction of parent molecule norfloxacin with topoisomerase IV; this observation underscores superiority of norfloxacin salts over norfloxacin in tackling fluoroquinolone‐resistant strain of S. aureus .…”

Section: Discussionmentioning

confidence: 97%

Norfloxacin salts of carboxylic acids curtail planktonic and biofilm mode of growth in ESKAPE pathogens

et al. 2018

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Synthesis and antibacterial activity of conjugates between norfloxacin and analogues of the siderophore vanchrobactin

Cited by 37 publications

References 27 publications

Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies

Investigating the Biosynthesis of Natural Products from Marine Proteobacteria: A Survey of Molecules and Strategies

Bacterial RNAP Inhibitors: Synthesis and Evaluation of Prodrugs of Aryl‐ureidothiophene‐carboxylic acids

Norfloxacin salts of carboxylic acids curtail planktonic and biofilm mode of growth in ESKAPE pathogens

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